4-Methyl-5-(2-hydroxyethyl)thiazole → 5-(2-Methanesulfonyl-ethyl)-4-methyl-thiazole

HRID 1271839Notes

Reaction equation

HRID 1271839 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].C(Cl)Cl.O[CH2:10][CH2:11][C:12]1[S:16][CH:15]=[N:14][C:13]=1[CH3:17].C(N(CC)CC)C>O>[CH3:1][S:2]([CH2:10][CH2:11][C:12]1[S:16][CH:15]=[N:14][C:13]=1[CH3:17])(=[O:4])=[O:3]

Participants

6

Reactant 4

HCID 11364-Methyl-5-(2-hydroxyethyl)thiazoleHCID 6344DichloromethaneHCID 8471TriethylamineHCID 31297Methanesulfonyl chloride

Product 1

HCID 184554425-(2-Methanesulfonyl-ethyl)-4-methyl-thiazole

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Methanesulfonyl chloride (5.4 mmol) was added to a methylene chloride (0.2 M) solution of 5-(2-hydroxyethyl)-4-methyl-thiazole (4.5 mmol) and triethylamine (23 mmol), and stirred at room temperature overnight. The mixture was poured into water and extracted with methylene chloride. The organic extracts were washed with NaHCO3 (sat), and the product was extracted with 1M aq. HCl. The aqueous extracts were neutralized with NaHCO3 (sat) and then extracted with methylene chloride. The organic extracts were dried (MgSO4) and filtered. Solvent removal afforded product (5).

Workup

  1. extractionextracted with methylene chloride
  2. washThe organic extracts were washed with NaHCO3 (sat)
  3. extractionthe product was extracted with 1M aq. HCl
  4. extractionextracted with methylene chloride
  5. dry with materialThe organic extracts were dried (MgSO4)
  6. filtrationfiltered
  7. customSolvent removal

Sources & evidence

ORD record
ord-e5f5df2de5ec4fc2acf367b4611fedff
Source dataset
uspto-grants-2007_04
Patent number
US07208488B2

Reaction notes

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